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Triethylamine → N-[3-(3,4-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-4-fluorobenzamide

HRID 548203
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 548203
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[F:12][C:13]([F:37])([F:36])[C:14]1[CH:15]=[C:16]([CH:29]=[C:30](C(F)(F)F)[CH:31]=1)[CH2:17][O:18][CH2:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][NH2:22].C(N(CC)CC)C>C(Cl)Cl>[F:36][C:13]([F:37])([F:12])[C:14]1[CH:15]=[C:16]([CH:29]=[CH:30][C:31]=1[C:13]([F:37])([F:36])[F:12])[CH2:17][O:18][CH2:19][CH:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][NH:22][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride

Produkt 1

HCID 86624052N-[3-(3,4-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-4-fluorobenzamideAusbeute 188,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A solution of 4-fluorobenzoyl chloride (1.2 mL, 10 mmol) in CH2Cl2 (20 mL) was dropped into a solution of the compound produced in Example 17 (3.31 g, 8.0 mmol) and triethylamine (2.8 mL, 20 mmol) in CH2Cl2 (50 mL) during 30 minutes under cooling with ice. After the solvent was evaporated therefrom in vacuo, water was added to the residue and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The residual oily product produced by evaporation of the solvent therefrom in vacuo was crystallized from petroleum ether to give the Compound 57 (3.76 g, 94%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. customAfter the solvent was evaporated
  3. additionin vacuo, water was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  7. customThe residual oily product produced by evaporation of the solvent
  8. customin vacuo was crystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-302690a9682642b394ab6888491b5004
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07939552B2

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